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ChemicalBook CAS DataBase List 3,4-diacetoxystyrene
57142-64-0

3,4-diacetoxystyrene synthesis

4synthesis methods
the preparation method of 3,4-diacetoxystyrene comprising: at a temperature of 60-70°C, 3,4-dihydroxybenzaldehyde and malonic acid in at least one organic solvent React under the condition that and catalyst exists, generate the first reaction mixture that comprises 3,4-dihydroxycinnamic acid; Be heated up to 80-90 ℃, make the first reaction mixture continue to react, generate the first reaction mixture that comprises 3,4-dihydroxystyrene The second reaction mixture; the second reaction mixture is purified to obtain 3,4-diacetoxystyrene; at a temperature of 10-20°C, 3,4-dihydroxystyrene reacts with an acetylating reagent to generate 3,4-dihydroxystyrene A third reaction mixture of diacetoxystyrene; purification of the third reaction mixture yields 3,4-diacetoxystyrene.[1]
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Yield:57142-64-0 87.3%

Reaction Conditions:

with 10H-phenothiazine;triethylamine in tert-butyl methyl ether at -5 - 20; for 1 h;Green chemistry;

Steps:

2 Example 2

Add 3,4-dihydroxystyrene (136 g) to a 2 L four-neck bottle. triethylamine (212g), phenothiazine (1.4g), methyl tert-butyl ether (544g), dry ice-ethanol bath to -5 to 0 °C, acetyl chloride (168 g) was added dropwise with stirring, and the internal temperature was controlled at -5 to 0 °C. After the completion of the dropwise addition, the temperature was raised at 10 to 20 °C to continue the reaction for 1 hour. sampling analysis (central control 1, raw material After completion of the reaction, the mixture was filtered, and the cake was washed with methyl t-butyl ether (50 g × 3). The filtrate was quenched by the addition of 8 g of methanol, and the reaction was stirred for 10 minutes. After completion, phenothiazine (1.4 g) was added, and the reaction liquid was concentrated, and methyl tert-butyl ether (580 g) was collected to obtain crude product (220 g). Crude recrystallized at low temperature the product 3,4-diacetoxystyrene (192 g) was obtained in a yield of 87.3%, and was analyzed by sampling (main content >97%).

References:

CN108911982,2018,A Location in patent:Paragraph 0046; 0047